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Preparation method for beach-chair-typed nonacene compounds

A benzene compound and chair-type technology, which is applied in the field of preparation of beach chair-type nonacene compounds, can solve the problem of no nonacene, etc., achieve narrow energy band gap, high carrier mobility, and improve the ability to be easily oxidized and deteriorated. Effect

Active Publication Date: 2018-06-08
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are relevant reports about linear nonacene in the prior art, but there is no relevant report about beach chair nonacene

Method used

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  • Preparation method for beach-chair-typed nonacene compounds
  • Preparation method for beach-chair-typed nonacene compounds
  • Preparation method for beach-chair-typed nonacene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthetic method of beach chair type nonacene adopts the following steps:

[0032] (1) Weigh CBr 4 (1.60g, 0.0048mol) was dissolved in 100mL toluene, stirred for 30min under nitrogen gas, and then PPh was added 3 (3.17g, 0.012mol), continue to keep N 2 Atmosphere, compound 1 (1.00 g, 0.0012 mol) was added after the color of the whole system turned light yellow. keep N 2 The atmosphere was heated to 80°C for 24h. After the reaction was completed, it was cooled to room temperature, and the reaction system was quickly suction-filtered, and the filtrate was spin-dried and then filtered through a fast silica gel column, and the filtrate was spin-dried to obtain compound 2.

[0033] (2) Weigh compound 2 (0.50g, 0.51mmol), phenylboronic acid (0.032g, 0.26mmol), potassium carbonate K 2 CO 3 (0.72g, 5.2mmol) in a sealed tube, add 50mL of toluene, 10mL of ethanol, 10mL of mixed solvent composed of water, nitrogen gas and stir for 30min, then add the catalyst Pd(PPh 3 )...

Embodiment 2

[0037] The synthetic method of beach chair type nonacene adopts the following steps:

[0038] (1) Weigh CBr 4 (2.40g, 0.0072mol) was dissolved in 100mL toluene, stirred for 20min under nitrogen gas, and then PPh was added 3 (4.76g, 0.018mol) continue to maintain N 2 Atmosphere, compound 1 (1.50 g, 0.0018 mol) was added after the color of the whole system turned light yellow. keep N 2 The atmosphere was heated to 110°C for 24h. After the reaction was completed, it was cooled to room temperature, and the reaction system was quickly suction-filtered, and the filtrate was spin-dried and then filtered through a fast silica gel column, and the filtrate was spin-dried to obtain compound 2.

[0039] (2) Weigh compound 2 (1.00g, 1.02mmol), phenylboronic acid (0.064g, 0.52mmol), potassium carbonate K 2 CO 3 (1.44g, 10.40mmol) in a sealed tube, add 60mL of toluene, 12mL of ethanol, 12mL of mixed solvent composition of water, nitrogen gas and stir for 40min, then add the catalyst Pd...

Embodiment 3

[0043] The synthetic method of beach chair type nonacene adopts the following steps:

[0044] (1) Take CBr 4 Dissolve in toluene, stir for 30min under nitrogen gas, then add PPh 3 continue to keep N 2 Atmosphere, compound 1 was added after the color of the whole system turned light yellow. keep N 2 The atmosphere was heated to 80°C for 24h. After the reaction was completed, it was cooled to room temperature, and the reaction system was quickly suction-filtered, and the filtrate was spin-dried and then filtered through a fast silica gel column, and the filtrate was spin-dried to obtain compound 2.

[0045] (2) Dissolve compound 2, phenylboronic acid, and potassium carbonate in a mixed solvent of toluene, ethanol, and water with a volume ratio of 5:1:1 after anaerobic treatment under a nitrogen atmosphere, and the catalyst Pd (PPh 3 ) 4 Compound 3 was obtained through a coupling reaction. The amount of catalyst used is 10 mol% of the total amount of raw materials, the rea...

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Abstract

The present invention relates to a preparation method for beach-chair-typed nonacene compounds. The method comprises the following steps: under the protection of an inert gas, 6-(bis(4-(dodecoxy)phenyl)methylene)-13-(bromo(phenyl)methylene)-6,13-dihydropentacene and 1,4-benzenediboronic acid pinacol diester are dissolved into an appropriate solvent, under the action of a catalyst, through a coupling reaction, 1,4-di((13-(bis(4-(dodecyl)phenyl)methylene)dihydropentacene-6(13H)-phenylmethylene)benzene is obtained, then under the action of an iodine element, irradiation is performed by using an ultraviolet mercury lamp, and through a photocyclization reaction, the final product c-HBC dimers, namely, the beach-chair-typed nonacene derivatives are obtained. According to the method provided by the invention, the excellent-performance stable beach-chair-typed nonacene derivatives are synthesized for the first time, and the compounds can be used in the fields such as organic field effect transistors, organic light emitting diodes and organic solar cells.

Description

technical field [0001] The invention relates to a synthesis method of acene substances, in particular to a preparation method of a beach chair type nonacene compound. Background technique [0002] Acenes are an important class of organic compounds. The smallest acene species—anthracene—is a stable and well-known synthetic fragment. As organic semiconductor materials, tetracene and pentacene are widely used in fields such as organic field-effect transistors, organic light-emitting diodes, and organic solar cells. Larger acenes such as hexacene, heptacene, octacene, and nonacene are a more interesting class of conjugated compounds. They have narrow band gaps and high electron mobility, but they are easily oxidized. Higher-order acene substances theoretically have an open-shell singlet ground state, and the existence of free radicals will strengthen the extension of molecular size. The increase in free radicals makes the synthesis of longer acenes more challenging. Current...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/20C07C41/32C07C41/30C07C43/225C07C43/215
CPCC07B2200/09C07C41/30C07C41/32C07C43/225C07C43/215C07C43/20
Inventor 肖胜雄毕萌于璇叶雨萌刘泰峰王安妮韩颖颖
Owner SHANGHAI NORMAL UNIVERSITY
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